Last year I sold my business for $52,000,000.

Last year I sold my business for $52,000,000. Here's every idea I tried before my big win. 1. At 15 I launched a drop shipping car parts business. We fail, but learn a lot. 2. A rendering firm for architects. I hire a team in the Philippines. Good money, nothing crazy. 3. I pour all my extra money into iPhone app ideas. All fail. 4. Project management software. I raise 100k, drop out of college, move to South America, then St. Louis. I live cheaply to fund it. 5. I find a group in China that can replicate oil paintings perfectly. Upload your face, then get a hand-painted original. Hilarious. 6. New bedding concept that allows you to never make your bed again. I meet John on Twitter, we team up, we raise 50k in pre-orders. 7. We pivot our project management software to a team productivity app. Metala acquires us, I move to Canada. Small win. Kicked out of Canada, unable to get a work visa, back to St. Louis. 8. Jon and I have a ton of product ideas, so we form Need/Want, a startup studio to crank them out. 9. Paper notebook with a pre-paid shipping envelope inside. When you finish the notebook, we scan and digitize, then sync to a companion app. 10. We create the original super thin iPhone case and call it Peel. 11. Our original bedding manufacturer takes our money and never delivers. We piece together 100k and relaunch as Primary Goods, using premium linen. 12. Emojis as Halloween masks. We're first to do it Halloween 2014. Goes viral, tons of press. We make 50k in 60 days. That money saves the bedding business. 13. Back to Peel. We do cases for every iPhone and Android generation. I end up owning it for 10 years. We do super thin wireless chargers, wallet concept, magnetic notebook, the touch tool, and many more products. 14. Favorite things of interesting people. Media company. It's all affiliate links. 15. Short-term rentals. Company goes through a tough period, so I start Airbnb-ing my loft. It crushes. I tell myself, if I could just find 10 more. 16. I find 10 more. We buy a historic building in downtown St. Louis. I use all the money I have and even sell my car. We convert it into 14 short-term rentals and 9 offices. 17. My Second. It's a virtual assistant you can text with. It's all before AI, real humans on the back end. Hard business, we shut down. 18. Supplies for Airbnb hosts. Doesn't go anywhere. 19. We buy an e-commerce business and lose 700k. Sue the buyers, total mess, lots of lessons. 20. Shepherd. This is the one. We help small businesses hire amazing remote staff overseas. In four years, we're 150 employees in The Philippines, Latin America, and South Africa, and very profitable. I take an offer to sell majority at a 52 million dollar valuation. We later rename it somewhere.com. That's 20 years of building, failing, learning. Ups and downs. The lesson: stay in the game, parlay your wins, and keep building.